fix: add smtp ssl

[mubashir1osmani]

Relevant issues

LIT-2665

uses SSL by default - user would only have to configure smtp as stated in these docs

Linear ticket

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• I have added meaningful tests
• My PR passes all unit tests on make test-unit
• My PR's scope is as isolated as possible; it only solves 1 specific problem
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CI (LiteLLM team)

CI status guideline:

• 50-55 passing tests: main is stable with minor issues.
• 45-49 passing tests: acceptable but needs attention
• <= 40 passing tests: unstable; be careful with your merges and assess the risk.

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Screenshots / Proof of Fix

Type

🆕 New Feature
🐛 Bug Fix
🧹 Refactoring
📖 Documentation
🚄 Infrastructure
✅ Test

Changes

[greptile-apps]

Greptile Summary

This PR fixes a hang when users configure LiteLLM's SMTP integration against a server that requires implicit SSL (port 465). It extracts two helpers — _should_use_smtp_ssl and _create_smtp_connection — and correctly skips starttls() when SMTP_SSL is used, since calling starttls() on an already-SSL connection raises SMTPNotSupportedError.

• _should_use_smtp_ssl returns True for port 465 or when SMTP_USE_SSL=True is set; existing STARTTLS (port 587) behaviour is unchanged.
• The send_email function now wraps connection creation through the helper and guards starttls() with not isinstance(server, smtplib.SMTP_SSL).
• Three unit tests are added for _should_use_smtp_ssl; _create_smtp_connection itself has no test asserting which constructor is called.

Confidence Score: 4/5

Safe to merge; the change is narrowly scoped to SMTP connection setup and does not touch the request-handling or auth paths.

The logic for choosing between SMTP_SSL and plain SMTP is correct, the isinstance guard before starttls() is necessary and present, and port-587 users see no behaviour change. The only gap is that _create_smtp_connection lacks a direct test to verify it returns the right connection type.

tests/test_litellm/proxy/test_proxy_utils.py — a test for _create_smtp_connection would improve coverage of the actual branching logic.

Important Files Changed

Filename	Overview
litellm/proxy/utils.py	Extracts _should_use_smtp_ssl and _create_smtp_connection helpers; skips starttls() when SMTP_SSL is used; fixes hang on port 465 implicit-SSL servers
tests/test_litellm/proxy/test_proxy_utils.py	Adds three unit tests for _should_use_smtp_ssl covering port 465, explicit SMTP_USE_SSL=True, and port 587; _create_smtp_connection itself is not tested

_{Reviews (1): Last reviewed commit: "add smtp ssl" | Re-trigger Greptile}

[codecov]

Codecov Report

✅ All modified and coverable lines are covered by tests.

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[veria-ai]

PR overview

All previously flagged issues have been addressed. No open security concerns remain on this pull request.

Security review

No open security issues remain on this pull request.

Fixed/addressed: 2 · PR risk: 0/10

[yassin-berriai]

veria score is 7/10. fix ci issues and get acceptable veria score